Ethyl Acetate → HCID 54334081, compound

HRID 1417562Notes

Reaction equation

HRID 1417562 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[Br:5][C:6]1[CH:7]=[C:8]([CH:16](Br)[C:17]([CH3:19])=O)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO>[NH2:1][C:2]1[S:3][C:16]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:14])[CH3:15])=[C:6]([Br:5])[CH:7]=2)=[C:17]([CH3:19])[N:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 53935881HCID 53935881, compound

Product 1

HCID 54334081HCID 54334081, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

Thiourea (65 mg, 0.857 in mol) was added to 1-(3-bromo-4-isopropoxyphenyl)-1-bromo acetone (200 mg, 0.571 mmol) in 0.5 mL of methanol and the mixture was heated to 40° C. The mixture was then heated to 80° C. And 1.0 mL of methanol was added to facilitate stirring. After refluxing 3 h, the reaction was transferred to a separatory funnel with 50 mL of ethyl acetate and 30 mL of saturate aqueous sodium bicarbonate, the layers were separated, and the organic layer was washed with 30 mL of brine. Drying over sodium sulfate and evaporation gave the crude product. Purification by flash chromatography, eluting with 30-50% ethyl acetate in hexane, gave 124 mg of the title compound as a white solid. Mass spectrum (NH3/CI): m/z=327 (M+1).

Workup

  1. temperatureThe mixture was then heated to 80° C
  2. temperatureAfter refluxing 3 h
  3. customthe layers were separated
  4. washthe organic layer was washed with 30 mL of brine
  5. dry with materialDrying over sodium sulfate and evaporation
  6. customgave the crude product
  7. customPurification by flash chromatography
  8. washeluting with 30-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1c682981999b40caba3671e4f2594a6b
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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